U.S. Pat. No. 2,273,564 discloses a process to synthesize substituted 1,4-diaminobenzene compounds with a substituent on the 2 position. U.S. Pat. No. 6,648,923 B1 discloses a process to synthesize 2-methoxymethyl-1,4-benzenediamine and the salts thereof.
The previous syntheses described above to reach 2-methoxymethyl-1,4-benzenediamine (IV-a), its derivatives, and the salts thereof are not completely satisfactory.
Therefore, there is a need for a simple, industrially applicable, efficient, not expensive and high yield process to synthesize of 2-methoxymethyl-1,4-benzenediamine (IV-a), its derivatives of formula (IV), and the salts thereof.
The key step of the process of this invention is a reductive amination involving preparation of the quinone monoxime (e.g. 2-methoxymethylnitrosophenol) as a key intermediate.